BRPI0507076A - substituted quinolines and their use as mycobacterial inhibitors - Google Patents

substituted quinolines and their use as mycobacterial inhibitors

Info

Publication number
BRPI0507076A
BRPI0507076A BRPI0507076-7A BRPI0507076A BRPI0507076A BR PI0507076 A BRPI0507076 A BR PI0507076A BR PI0507076 A BRPI0507076 A BR PI0507076A BR PI0507076 A BRPI0507076 A BR PI0507076A
Authority
BR
Brazil
Prior art keywords
alkyl
hydrogen
het
alkyloxy
hydroxy
Prior art date
Application number
BRPI0507076-7A
Other languages
Portuguese (pt)
Inventor
Jerome Emile George Guillemont
Elisabeth Ther Se Jea Pasquier
Original Assignee
Janssen Pharmaceutica Nv
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv
Publication of BRPI0507076A publication Critical patent/BRPI0507076A/en
Publication of BRPI0507076B1 publication Critical patent/BRPI0507076B1/en
Publication of BRPI0507076B8 publication Critical patent/BRPI0507076B8/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5355—Non-condensed oxazines and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A61P31/06—Antibacterial agents for tuberculosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Pulmonology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

QUINOLINAS SUBSTITUìDAS E SEU USO COMO INIBIDORES MICOBACTERIANOS. A presente invenção refere-se a novos derivados de quinolina substituida de acordo com a fórmula geral (la) ou com a fómula geral (lb) bem como a sais, amina quaternárias, formas estereoquimicamente isoméricas, formas tautoméricas e formas de N-óxido desses derivados, onde R¬ 1¬ é hidrogênio, halo, haloalquila, ciano, hidróxi, Ar, Het, alquila, alquilóxi, alquilito, alquiloxialquila, alquiltioalquila, Ar-alquila ou di(Ar)alquila; p é 1, 2, 3 ou 4; R¬ 2¬ é hidrogênio, hidróxi, tio, alquilólxi, alquiloxialquilóxi, alquiltio, mono ou di(alquil)amino ou um radical de fórmula ; R¬ 3¬ é alquila, Ar, Ar-alquila, Het ou Het-alquila; R¬ 4¬ é hidrogênio, alquila ou benzila; R¬ 5¬ é hidrogênio, halo, haloalquila, hidróxi, Ar, alquila, alquilóxi, alquiltio, alquiloxialquila, alquiltioalquila, Ar-alquila ou di(Ar)alquila; ou dois radicais vicinais R¬ 5¬ poderão ser tornados juntos para formar juntamente com o anel fenila ao qual se ligam uma naftila; r é 1,2,3,4 ou 5; R¬ 6¬ é hidrogênio, alquila, Ar ou Het; R¬ 7¬ é hidrogênio ou alquila; R¬ 8¬ é oxo; ou R¬ 7¬ e R¬ 8¬ tomados juntos formam o radical -CH<154>CH-N<154>; Z é CH~ 2~ ou C(<154>O). Os compostos reivindicados são úteis para o tratamento de doenças micobacterianas, particularmente aquelas doenças causadas por micobactérias patogênicas tais como M. tuberculosis, M.bovis, M. avium, M. smegmatis e M. marinum. Também são reivindicados uma composição farmacêutica que contém um composto da presente invenção, o uso dos compostos ou composições reivindicados para a produção de um medicamento para o tratamento de doenças micobacterianas e um processo para preparar os compostos reivindicados.REPLACED QUINOLINES AND THEIR USE AS MYCOBACTERIAL INHIBITORS. The present invention relates to novel substituted quinoline derivatives according to general formula (Ia) or general formula (Ib) as well as salts, quaternary amine, stereochemically isomeric forms, tautomeric forms and N-oxide forms thereof. derivatives, wherein R 1 is hydrogen, halo, haloalkyl, cyano, hydroxy, Ar, Het, alkyl, alkyloxy, alkylite, alkyloxyalkyl, alkylthioalkyl, Ar-alkyl or di (Ar) alkyl; p is 1, 2, 3 or 4; R 2 is hydrogen, hydroxy, thio, alkyloxy, alkyloxyalkyloxy, alkylthio, mono or di (alkyl) amino or a radical of formula; R¬ 3¬ is alkyl, Ar, Ar-alkyl, Het or Het-alkyl; R¬ 4¬ is hydrogen, alkyl or benzyl; R 5 is hydrogen, halo, haloalkyl, hydroxy, Ar, alkyl, alkyloxy, alkylthio, alkyloxyalkyl, alkylthioalkyl, Ar-alkyl or di (Ar) alkyl; or two vicinal radicals R 5 may be joined together to form together with the phenyl ring to which a naphthyl attaches; r is 1,2,3,4 or 5; R¬6¬ is hydrogen, alkyl, Ar or Het; R¬ 7¬ is hydrogen or alkyl; R 8 is oxo; or R¬7¬ and R¬8¬ taken together form the radical -CH <154> CH-N <154>; Z is CH ~ 2 ~ or C (<154> O). The claimed compounds are useful for the treatment of mycobacterial diseases, particularly those diseases caused by pathogenic mycobacteria such as M. tuberculosis, M. bovis, M. avium, M. smegmatis and M. marinum. Also claimed are a pharmaceutical composition containing a compound of the present invention, the use of the claimed compounds or compositions for the manufacture of a medicament for the treatment of mycobacterial diseases and a process for preparing the claimed compounds.

BRPI0507076A 2004-01-23 2005-01-21 substituted quinolines, their preparation process, pharmaceutical composition comprising them and their use as mycobacterial inhibitors BRPI0507076B8 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US53876804P 2004-01-23 2004-01-23
US60/538,768 2004-01-23
PCT/EP2005/050267 WO2005070924A1 (en) 2004-01-23 2005-01-21 Substituted quinolines and their use as mycobacterial inhibitors

Publications (3)

Publication Number Publication Date
BRPI0507076A true BRPI0507076A (en) 2007-06-19
BRPI0507076B1 BRPI0507076B1 (en) 2019-06-25
BRPI0507076B8 BRPI0507076B8 (en) 2021-05-25

Family

ID=34807224

Family Applications (1)

Application Number Title Priority Date Filing Date
BRPI0507076A BRPI0507076B8 (en) 2004-01-23 2005-01-21 substituted quinolines, their preparation process, pharmaceutical composition comprising them and their use as mycobacterial inhibitors

Country Status (20)

Country Link
US (1) US7338949B2 (en)
EP (1) EP1711492B1 (en)
JP (1) JP4773975B2 (en)
KR (1) KR101150172B1 (en)
CN (1) CN1910177B (en)
AP (1) AP2188A (en)
AT (1) ATE392423T1 (en)
AU (1) AU2005206330B2 (en)
BR (1) BRPI0507076B8 (en)
CA (1) CA2553266C (en)
DE (1) DE602005006101T2 (en)
EA (1) EA011359B1 (en)
ES (1) ES2306082T3 (en)
HK (1) HK1100927A1 (en)
IL (1) IL177013A0 (en)
NO (1) NO337705B1 (en)
NZ (1) NZ547277A (en)
UA (1) UA85570C2 (en)
WO (1) WO2005070924A1 (en)
ZA (1) ZA200606070B (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1713776B1 (en) * 2004-01-29 2008-05-14 Janssen Pharmaceutica N.V. Quinoline derivatives for use as mycobacterial inhibitors
EE05697B1 (en) 2005-06-08 2014-02-17 Janssen Pharmaceutica N.V. Quinoline derivatives as antibacterial agents
JO2855B1 (en) 2005-08-03 2015-03-15 شركة جانسين فارماسوتيكا ان. في Qunioline Derivatives as Antibacterial Agents
JO2837B1 (en) * 2005-08-03 2014-09-15 جانسن فارمسيتكا ان في Quinoline Derivatives as Antibacterial Agents
US8686002B2 (en) 2005-08-21 2014-04-01 AbbVie Deutschland GmbH & Co. KG Heterocyclic compounds and their use as binding partners for 5-HT5 receptors
JO3271B1 (en) 2006-12-06 2018-09-16 Janssen Pharmaceutica Nv Antibacterial Quinoline Derivatives
JO2970B1 (en) 2006-12-06 2016-03-15 جانسين فارماسوتيكا ان. في Antibacterial Quinoline Derivatives
JO2684B1 (en) * 2006-12-06 2013-03-03 جانسين فارماسوتيكا ان في Antibacterial Quinoline Derivatives
JO2685B1 (en) 2006-12-06 2013-03-03 جانسين فارماسوتيكا ان في Antibacterial Quinoline Derivatives
CA2711912A1 (en) * 2008-01-14 2009-07-23 Jyoti Chattopadhyaya Quinoline, naphthalene and conformationally constrained quinoline or naphthalene derivates as anti-mycobacterial agents
ES2576491T3 (en) * 2012-04-27 2016-07-07 Janssen Pharmaceutica, N.V. Quinoline Antibacterial Derivatives
MX358506B (en) * 2012-04-27 2018-08-22 Janssen Pharmaceutica Nv Antibacterial quinoline derivatives.
AU2016255724B2 (en) * 2015-04-29 2020-05-14 The State of Israel, Ministry of Agriculture and Rural Development Agricultural Research Organization (ARO) (Volcani Center) Anti-phytopathogenic compositions

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001503411A (en) * 1996-10-28 2001-03-13 ディパートメント オブ ジ アーミー，ユー．エス．ガバメント Compounds, compositions and methods for the treatment of antibiotic resistant infections
JP4209472B2 (en) * 1997-06-02 2009-01-14 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ (Imidazole-5-yl) methyl-2-quinolinone derivatives as inhibitors of smooth muscle cell proliferation
US6103905A (en) * 1997-06-19 2000-08-15 Sepracor, Inc. Quinoline-indole antimicrobial agents, uses and compositions related thereto
JP2002505689A (en) * 1997-06-19 2002-02-19 セプレイコー インコーポレイテッド Quinoline-indole antimicrobial agents, uses and compositions related thereto
WO2001062234A2 (en) * 2000-02-24 2001-08-30 Janssen Pharmaceutica N.V. Dosing regimen
DE60134762D1 (en) * 2000-10-02 2008-08-21 Janssen Pharmaceutica Nv METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS
DK2301544T3 (en) 2002-07-25 2013-01-02 Janssen Pharmaceutica Nv Quinoline derivatives as intermediates for mycobacterial inhibitors

Also Published As

Publication number Publication date
KR20060127016A (en) 2006-12-11
BRPI0507076B1 (en) 2019-06-25
UA85570C2 (en) 2009-02-10
NZ547277A (en) 2009-08-28
KR101150172B1 (en) 2012-05-25
DE602005006101D1 (en) 2008-05-29
EA200601363A1 (en) 2006-12-29
JP4773975B2 (en) 2011-09-14
NO337705B1 (en) 2016-06-06
ZA200606070B (en) 2007-12-27
US20070082895A1 (en) 2007-04-12
NO20063747L (en) 2006-08-22
EP1711492A1 (en) 2006-10-18
AP2188A (en) 2010-12-14
HK1100927A1 (en) 2007-10-05
AP2006003693A0 (en) 2006-08-31
IL177013A0 (en) 2006-12-10
CA2553266C (en) 2013-03-12
WO2005070924A1 (en) 2005-08-04
CA2553266A1 (en) 2005-08-04
EP1711492B1 (en) 2008-04-16
CN1910177A (en) 2007-02-07
ES2306082T3 (en) 2008-11-01
WO2005070924A8 (en) 2006-05-11
DE602005006101T2 (en) 2009-07-02
CN1910177B (en) 2010-05-05
ATE392423T1 (en) 2008-05-15
JP2007518775A (en) 2007-07-12
EA011359B1 (en) 2009-02-27
AU2005206330A1 (en) 2005-08-04
AU2005206330B2 (en) 2010-09-16
BRPI0507076B8 (en) 2021-05-25
US7338949B2 (en) 2008-03-04

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Legal Events

Date Code Title Description
B07D Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette]
B06F Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]
B07E Notification of approval relating to section 229 industrial property law [chapter 7.5 patent gazette]

Free format text: NOTIFICACAO DE ANUENCIA RELACIONADA COM O ART 229 DA LPI

B06A Patent application procedure suspended [chapter 6.1 patent gazette]
B09A Decision: intention to grant [chapter 9.1 patent gazette]
B16A Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]

Free format text: PRAZO DE VALIDADE: 10 (DEZ) ANOS CONTADOS A PARTIR DE 25/06/2019, OBSERVADAS AS CONDICOES LEGAIS. (CO) 10 (DEZ) ANOS CONTADOS A PARTIR DE 25/06/2019, OBSERVADAS AS CONDICOES LEGAIS

B16C Correction of notification of the grant [chapter 16.3 patent gazette]

Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 21/01/2005 OBSERVADAS AS CONDICOES LEGAIS. PATENTE CONCEDIDA CONFORME ADI 5.529/DF

B21F Lapse acc. art. 78, item iv - on non-payment of the annual fees in time

Free format text: REFERENTE A 17A ANUIDADE.

B24J Lapse because of non-payment of annual fees (definitively: art 78 iv lpi, resolution 113/2013 art. 12)

Free format text: EM VIRTUDE DA EXTINCAO PUBLICADA NA RPI 2654 DE 16-11-2021 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDA A EXTINCAO DA PATENTE E SEUS CERTIFICADOS, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013.